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1-Chloro-2,3,4-trinitrobenzene

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Identification
Molecular formula
C6H2ClN3O6
CAS number
121-18-6
IUPAC name
1-chloro-2,3,4-trinitro-benzene;1-chloro-2,3,5-trinitro-benzene;2-chloro-1,3,4-trinitro-benzene
State
State

At room temperature, 1-Chloro-2,3,4-trinitrobenzene is a solid. It remains stable under normal conditions, typically requiring controlled conditions for safe handling due to its reactive nature.

Melting point (Celsius)
78.00
Melting point (Kelvin)
351.15
Boiling point (Celsius)
311.00
Boiling point (Kelvin)
584.15
General information
Molecular weight
232.55g/mol
Molar mass
232.5510g/mol
Density
1.7905g/cm3
Appearence

1-Chloro-2,3,4-trinitrobenzene appears as a yellow crystalline solid. It forms needle-like crystals and has an intense coloration due to the presence of nitro groups attached to the aromatic ring.

Comment on solubility

Solubility of 1-chloro-2,3,4-trinitro-benzene, 1-chloro-2,3,5-trinitro-benzene, and 2-chloro-1,3,4-trinitro-benzene

The solubility of nitro-substituted aromatic compounds, such as 1-chloro-2,3,4-trinitro-benzene, 1-chloro-2,3,5-trinitro-benzene, and 2-chloro-1,3,4-trinitro-benzene, tends to be influenced by several factors:

  • Polarity: Nitro groups (-NO2) are polar and can engage in hydrogen bonding with solvents, which may enhance solubility in polar solvents.
  • Chlorine Substitution: The presence of chlorine atoms can introduce steric hindrance and affect the overall polarity of the molecules, often rendering them less soluble in nonpolar solvents.
  • Temperature: Increased temperature generally increases solubility, allowing for more efficient interaction between solute and solvent molecules.

When considering solubility in water, these specific trinitro compounds are typically considered to be poorly soluble due to their hydrophobic aromatic character combined with multiple nitro groups that can lead to increased molecular weight and reduced solvation.

However, these compounds often demonstrate improved solubility in organic solvents such as:

  • Dimethyl sulfoxide (DMSO)
  • Ethanol
  • Acetone

In summary, while the trinitrobenzene derivatives have limited solubility in water, their solubility can significantly vary in different organic solvents owing to the intricate balance of their structural features.

Interesting facts

Interesting Facts about 1-chloro-2,3,4-trinitro-benzene, 1-chloro-2,3,5-trinitro-benzene, and 2-chloro-1,3,4-trinitro-benzene

These compounds, known as chlorinated trinitrobenzenes, are fascinating members of the nitroaromatic family. Each variant features unique substitutions that contribute to distinct chemical behaviors and properties.

Key Characteristics

  • Explosive Potential: The presence of nitro groups (-NO2) makes these compounds highly explosive. They are often studied in the context of energetic materials.
  • Structural Variability: The chlorination and nitration patterns in these compounds lead to differences in reactivity, polarity, and stability, making them interesting for pharmacological and industrial applications.
  • Environmental Impact: Nitroaromatic compounds are persistent pollutants. Their breakdown products can have significant effects on soil and water quality, thus raising concerns about their environmental impact.

Chemical Applications

Chlorinated trinitrobenzenes have applications in various fields:

  • As Intermediates: These compounds are precursors in the synthesis of dyes, pharmaceuticals, and agrochemicals.
  • In Explosives Research: Due to their explosive characteristics, they are often used in the study of pyrotechnics and propellants.
  • In Analytical Chemistry: They serve as standard reference materials for various analytical methods due to their distinct reactivity.

Safety Considerations

Handling these compounds requires caution. They are classified as hazardous materials due to their explosive nature and potential health risks upon exposure:

  • Toxicity: They can be harmful if inhaled or ingested, necessitating strict safety protocols.
  • Stability Issues: Their susceptibility to detonation highlights the need for careful storage and handling to prevent accidental explosions.

Overall, 1-chloro-2,3,4-trinitro-benzene, 1-chloro-2,3,5-trinitro-benzene, and 2-chloro-1,3,4-trinitro-benzene are not only intriguing compounds because of their structural diversity and chemical properties but also significant for their various applications in science and industry.

Synonyms
SCHEMBL9416495